🎃 So Many Halloween Paddles, So Little Time… Which One Do You Choose?
- supfrederick
- Sep 22
- 5 min read
Sep 20, 2025
Every fall, the rivers and lakes around us transform into something magical. The water shimmers with sunset colors, the air gets crisp, and paddlers swap their usual gear for witches’ hats, brooms, and skeleton suits.
This year, our local paddleboarding and kayaking community is spoiled for choice. There are more Halloween-themed paddles than ever before, some right here in Maryland, others just a short drive into DC or Annapolis. The real challenge? Deciding which one to attend.
We’ve rounded up the who, what, where, when, and how of each major event so you can plan your spooky season on the water.
So many to choose from!
Here are our favorites!
🧙🧹 Paddle DMV’s 4th Annual Witch & Warlock Paddle
For more details: See event page for details.
Who: Open to all paddlers (SUP, kayak, canoe) just bring your best witch or warlock costume, or come dressed in all black.
What: A large-scale gathering of pointy hats and flowing robes filling the water with witchy flair. Expect photo-worthy group shots and a strong community vibe.
How: RSVP online via the Facebook event. Costumes encouraged, safety gear required.
When: Sat, Oct 25, 2025, 11:00 AM–1:00 PM, Meet/Launch: Columbia Island Marina (Potomac “Pentagon Lagoon”); along the George Washington Memorial Parkway.
What to expect: A big coven-style paddle pointy hats, capes, group photos, and post-paddle bites nearby.
Great for shore-side families:
Georgetown Waterfront Park / Washington Harbour boardwalk; wide river views and easy stroller access.
Columbia Island Marina walkway / Island Time area for close-up views of the launch and returns.
This one’s become a regional tradition, drawing paddlers from across the DMV. If you love big groups and dramatic visuals, this is your moment to shine (or cackle). This is an oh so spooky favorite!
🦇Sixth Annual Freaky Flotilla — Halloween Social Paddle (Annapolis, MD)
Who: Paddlers of all ages and skill levels.
What: A flotilla-style paddle—a true Halloween tradition. Hundreds of people dress up and take to the water in costume.
Where: Details here.
How: Register in advance, join the flotilla, and bring your best spooky vibes.
When: Sun, Oct 19, 2025, 10:00 AM–12:00 PM (See Facebook page for exact schedule), Meet/Launch: Truxtun Park / Truxtun Park Boat Ramp (Annapolis).
What to expect: One of the area’s longest-running Halloween flotillas—lots of boats, lots of costumes.
Great for shore-side families:
Truxtun Park areas near the public boat ramp (follow city signage) for launch/finish views.
If you want to feel like you’re part of something big and legendary, this is the event. The Freaky Flotilla is one of the most established paddles of the season.
👻 B’More SUP — Halloween Paddle Palooza (Essex, MD)
Who: A fun-loving crew of paddlers who take costumes seriously; think skeletons, pumpkins, and monsters galore.
What: A paddle party where the costumes are the main event. Music, laughter, and plenty of group photo opportunities.
Where: Check the event page here.
How: RSVP online and come ready to paddle in full Halloween spirit.
When: Sat, Oct 25, 2025, 11:00 AM, Meet/Launch: 2015 Turkey Point Rd, Essex (partnering with Eastern Watersports & Charly’s Waterfront).
What to expect: Big, goofy costume energy; lots of families and group pics on protected water.
Great for shore-side families:
Charly’s Waterfront lawn/boardwalk area by Sue Creek—easy viewing as paddlers pass by. (Use the address above to navigate.)
If you want festivity over formality, this is the one. It’s all about embracing your inner goofball, grabbing your friends, and celebrating Halloween on the water.
🎃 Capital SUP — Halloween Paddle (Annapolis, MD)
Who: Hosted by Capital SUP in Annapolis—expect a mix of regulars and newcomers to the local scene.
What: A structured paddle with Annapolis waterfront views. Costumes encouraged, and the community energy is always high.
Where: Capital SUP, Annapolis, MD.
How: Sign up directly with Capital SUP. Rentals may be available, so this is a good choice if you don’t want to haul your own board.
When: Full event info here; Sat, Oct 18, 2025, 9:30–11:00 AM; Meet/Launch: Amos Garrett Waterfront Park (101 Spa View Ave., on Spa Creek).
What to expect: A scenic out-and-back on Spa Creek with Capital SUP’s crew; costumes encouraged; rentals often available.
Great for shore-side families:
Amos Garrett Waterfront Park shoreline and small pier for close-up photos as the parade heads toward Downtown Annapolis.
This one gives you the best of both worlds, the fun of costumes with the scenic beauty of Annapolis. It’s a safe bet if you want something structured but still festive.
🧙♀️🍻Montgomery Parks — Witchy Paddle: Acoustics & Ales Edition (Boyds, MD)
Who: Hosted by Montgomery Parks. Perfect for those who like paddling and socializing.
What: A witchy paddle capped off with live acoustic music and local ales; costumes, of course, are welcome.
Where: Montgomery Parks (see the official event page for launch details).
How: Sign up through Montgomery Parks. Bring your own board or rent if available.
When: Sat, Oct 25, 2025, 4:00–7:00 PM (Witchy paddle begins ~4:30)…Times listed on the event page but, Meet/Launch: Black Hill Discovery Center, 20926 Lake Ridge Dr., Boyds (Little Seneca Lake). Registration required for the paddle.
What to expect: Sunset witchy paddle + campfire, s’mores, and live music—perfect “paddle + hang” evening.
Great for shore-side families:
Discovery Center lakefront has easy, kid-friendly shoreline to watch the parade and stay for music afterward.
This one is all about balance, enjoy your time on the water, then kick back with music and drinks. Perfect for anyone who wants a more social evening out.
Tips for families & first-timers (even if you’re not paddling)
Arrive 20–30 minutes early to claim a good shoreline spot for photos and costume viewing.
Parking: Use the event links above for day-of updates and parking notes; popular launch areas (Amos Garrett, Truxtun Park, Columbia Island Marina) can fill fast.
Strollers & snacks: Georgetown Waterfront Park, Black Hill Discovery Center, and most city parks listed have flat paths and benches.
Cheer section signs: Kids love waving to paddlers; homemade pumpkin or ghost signs are a hit in photos.
Safety: Keep little ones back from docks/ramps during launches; paddlers always yield to safety details in the events page, and paddlers, always listen to the Safety briefing, and keep an eye on the weather and currents!
Wind 💨 also loves capes and hats! Ask us how we know! (Lol) So it always helps to tie your hat on incase of high winds!
Please note: Times/locations above come directly from each organizer’s page; always check the event link the morning of for weather or schedule changes, then tag @SUP Frederick in your photos so we can share the magic with the community!
The privilege of our community is that we have so many options, and that means no matter where you end up, you’ll be part of the magic.
So, which one will it be this year? 🎃🧙♀️👻
✨ How Do You Choose?
Here’s the good news: you really can’t go wrong. Whether you’re after bigger crowds, and regional tradition (Freaky Flotilla, Witch & Warlock), goofy costumes (Paddle Palooza), scenic Annapolis (Capital SUP), or a mix of paddling + live music (Montgomery Parks), there’s something for everyone.
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